CA2671471C - Mild compositions for skin disinfection - Google Patents
Mild compositions for skin disinfection Download PDFInfo
- Publication number
- CA2671471C CA2671471C CA2671471A CA2671471A CA2671471C CA 2671471 C CA2671471 C CA 2671471C CA 2671471 A CA2671471 A CA 2671471A CA 2671471 A CA2671471 A CA 2671471A CA 2671471 C CA2671471 C CA 2671471C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- acid
- skin
- amino acid
- acylated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000004659 sterilization and disinfection Methods 0.000 title claims abstract description 17
- 150000001413 amino acids Chemical class 0.000 claims abstract description 44
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 36
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- 150000003839 salts Chemical class 0.000 claims abstract description 20
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- 125000000217 alkyl group Chemical group 0.000 claims description 14
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- 239000003795 chemical substances by application Substances 0.000 claims description 8
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A61K8/00—Cosmetics or similar toiletry preparations
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Abstract
The present invention discloses compositions for aqueous skin disinfection comprising hydrogen peroxide in a concentration of at least 0.1% to 10% (w/w), preferably 0.2-6%, and an N-acylated amino acid and/or peptide in the range of 0.1-20% (w/w), preferably 0.1-10%, more preferably 0.2-8%, and most preferably 0.2-5% (w/w). The N-acylated amino acid composition may be N-acylated glutamic acid and/or an N-acylated wheat protein hydrolysate, or a salt thereof.
Description
CA 2,671,471 Blakes Ref: 74537/00004
2 The present invention relates to mild and highly skin compatible, biocidally active
3 compositions for disinfection, sanitizing, antimicrobial regulation and sebum regulation of the
4 skin.
Human skin is permanently populated with a multitude of different microorgan-6 isms (bacteria, yeasts and fungi). The commensal microorganisms living on or in the skin may 7 form part of a microflora that is either resident (normal) or transient.
The resident microbial flora, 8 which is essential for good health of the skin, consists mainly of staphylococci (Staphylococcus 9 epidermis and Staphylococcus hominis), corynebacteria, Gram +
propionibacteria such as Propi-on/bacterium acnes, and also a yeast flora mainly composed of Pityrosporum ovale.
11 Pityrosporum ovale is for example believed to be involved in many skin disorders, such as seb-12 orrhoic dermatitis, folliculitis, confluent and reticulate papillomatosis and psoriatic lesions.
13 Most of the skin bacteria are present on the superficial squamous epidermis, col-14 onizing dead cells, and closely associated with the sebaceous and sweat glands. The excretions from these glands provide water, amino acids, urea, electrolytes and specific fatty 16 acids serving as nutrient elements mainly for Staphylococcus epidermidis and certain aerobic 17 corynebacteria.
18 Skin infections are usually caused by disruption of the ecological equilibrium of 19 the resident flora following colonization of the skin by pathogenic exogenous germs or following abnormal proliferation of an endogenous strain. The pathogenic germs that are the most com-21 mon are Pseudomonas aeruginosa (Gram), which is responsible for small spots, folliculitis, red 22 patches and pruritus, Candida alb/cans, which can cause inflammation at the labial angle, cuta-23 neous candidiasis, pruritus, folliculitis and aphthae, Staphylococcus aureus, which can cause 24 spots, folliculitis, impetigo and furuncles, and Group A Streptococci, responsible for impetigo.
In many industries, infection control and the prevention of spread of disease-26 causing micro-organisms is a major concern. In veterinary, healthcare, paramedical, hospitality, 27 food processing and industrial applications, the prevention of contamination with and spreading 28 of pathogenic microorganism is of crucial importance. Often, spreading of micro-organisms oc-29 curs via the hands. Viruses and bacteria on contaminated hands are easily spread among people in health care facilities such as hospitals. But also in washroom, health & wellness, 31 school and household applications, the maintenance of high hygiene standards is becoming 32 increasingly important.
22503483.3 1 CA 2,671,471 Blakes Ref: 74537/00004 1 Washing hands with detergents or soaps is a way to reduce the risk of infection.
2 However, in certain environments, such as hospitals or food processing, the required level of 3 disinfection cannot be achieved by commonly used soaps and detergents.
Consequently, hand 4 disinfectants have been developed to achieve higher levels of disinfection where the need ex-iStS.
6 Thus, this recent trend towards higher levels of infection control in hospital set-7 tings and in food & hospitality sectors, combined with the increasing awareness for infectious 8 diseases that can be transferred via the skin and respiratory system, have opted the industry to 9 come up with disinfecting compositions that can be used more frequently throughout the day.
These compositions must be hypoallergenic, non-toxic and not produce any undesirable residue 11 on the skin.
12 A problem with existing skin disinfection products, typically containing alcohols, 13 iodines/iodophors, chlorhexidine gluconate (CHG), phenolic compounds, triclosan, quaternary 14 ammonium compounds, or combinations thereof, is that they often sacrifice disinfectant activity for the sake of skin mildness or vice versa. For example, while raising the concentration of the 16 active ingredient may lead to a higher level of disinfection, such higher concentration frequently 17 leads to increased skin irritation, especially when frequently used.
Many of the currently availa-18 ble compounds cause skin dryness, skin irritation or are suspect for unwanted side-effects.
19 Many of the known and widely used skin disinfection compounds are under pressure or even banned from certain markets. This has caused the industry to come up with new solutions for 21 this problem.
22 An object of the invention is to provide an antimicrobial composition for use on 23 skin. It was found that the combination of hydrogen peroxide and N-acylated amino acids 24 and/or peptides, preferably having an acidic pH, provide for a mild yet highly effective disinfect-ant composition.
26 W092/21318 describes N-acyl derivatives of amino acids derived from cereal 27 protein hydrolysates, salts thereof, and cosmetic and detergent compositions containing said 28 derivatives or their salts.
29 EP 1 221 313 and WO 03/039496 describe detergent or cosmetic compositions having hydrating and preservative properties and simultaneously anti-dandruff and/or anti-odour 31 properties. The compositions of EP 1 221 313 comprise a salt of undecylenoil glutamate and/or 32 undecylenoil hydrolyzate of wheat and/or rice proteins and the compositions of WO 03/039496 22503483.3 2 CA 2,671,471 Blakes Ref: 74537/00004 1 include a capryloyl glutamate salt and/or capryloyl hydrolysate of wheat and/or rice protein.
2 Since such salts are able to perform also a preservative and hydrating effect, the compositions 3 do not need the addition of further preservative or hydrating agents or, at most, contain concen-4 trations thereof which are not efficacious per se. These compositions are not described for disinfecting the skin (i.e. instantly killing pathogenic micro-organisms) and are also not capable 6 of providing sufficient anti-microbial kill in sufficiently short contact times to produce an accepta-7 ble skin disinfection composition.
8 US2006/0024339 provides a method for managing redness of skin associated 9 with a dermatological condition, the method comprising topically administering to the skin of a patient a pharmaceutical composition comprising an extract of goji berries.
The pharmaceutical 11 composition used in these methods can further comprise at least one carboxylic acid. Optional-12 ly, the composition may contain various other components, among which at least one amino 13 acid or hydrogen peroxide. A useful amino acid may be N-acetylcystein.
However, the combine-14 tion of hydrogen peroxide and N-acetylcystein is not disclosed and no reference is made to the disinfecting or antimicrobial capacity of the compositions.
16 The use of lauroyl glutamate in an Emulsifying Natural System (Protelan ENS) 17 has been disclosed in a brochure of Protelan ENS (Zschimmer & Schwarz ltaliana S.p.A.; April 18 2002, BNSDOC IDNo. XP002431482). Protelan ENS is a blend of glyceryl stearate, cetearyl 19 alcohol, stearic acid and sodium lauroyl glutamate. In a series of stability and compatibility tests, an emulsion comprising 5% hydrogen peroxide in the water phase and 20%
Protelan ENS in the 21 oil phase was shown to provide a stable cream.
22 None of the prior art describes the high disinfection power of compositions as de-23 scribed herein. It was found that hydrogen peroxide and N-acylated amino acids separately 24 have low disinfection power, even in relatively high concentrations.
Only after combining hydro-gen peroxide and N-acylated amino acids in an aqueous system, a surprising synergistic effect 26 comes to effect. The synergy is highly significant and is totally unexpected when looking at the 27 performance of the two ingredients separately.
28 Thus, the present invention provides a composition for disinfecting skin compris-29 ing hydrogen peroxide in the range of 0.1-10% (w/w), preferably 0.2-6%, and an N-acylated amino acid and/or peptide in the range of 0.1-20% (w/w), preferably 0.1-10%, more preferably 31 0.2-8%, and most preferably 0.2-5% (w/w).
22503483.3 3 CA 2,671,471 Blakes Ref: 74537/00004 1 The term "N-acylated amino acid and/or peptide" according to the invention refers 2 to peptides and/or free amino acids, or salts thereof, wherein at least 50 % of the amino groups 3 of the free amino acids and/or of the peptides, is acylated. Preferably, all the amino groups are 4 acylated. The amino acid may be a single amino acid or may be a mixture of amino acids ob-tamable by hydrolysis of a suitable protein substrate. In the latter case, short peptides may be 6 present, typically comprising peptides with an average molecular weight lower than about 4000 7 Dalton, preferably lower than about 2000 Dalton.
8 The N-acylated peptide and/or N-acylated amino acid to be used according to the 9 invention preferably has a structure according to Formula I as follows:
11 R¨CO-N(H)-(CH2)n¨C(R')¨CO-X (I) 13 or a salt thereof, 14 wherein R-00- represents an acyl group wherein R is a saturated or unsaturated, straight of branched C5 to C21 radical, 16 n is 0, 1 or 2, 17 R' represents an amino acid side chain, and 18 X is OH or a group according to Formula II:
[NH¨CH(R')¨00-1, NH¨C(R')¨CO(OH) (II) 22 wherein m ranges from 0 to such a value that the compound of Formula II speci-23 fies a peptide having an average molecular weight of about 100 to about 3900 Dalton, 24 preferably of about 100 to about 1900 Dalton, more preferably about 100 to about 1300, most preferably about 100 to about 700 Dalton.
26 Suitable salts are those wherein the dissociated carboxylic groups are neutralised 27 with cations belonging to the group of alkaline metals and alkaline earth metals, ammonia, other 28 metals such as lead, iron, aluminum, manganese, copper, zinc, or by organic bases such as 22503483.3 4 CA 2,671,471 Blakes Ref: 74537/00004 1 arginine, lysine, mono-, di-, or triethanolamine, ornithine, histidine, morpholine, or choline. Such 2 neutralising cations can be utilised also in combinations with one another.
3 Preferably, the R moiety of the acyl group is a 06 to C20 radical. More preferred 4 are the straight chain variants thereof (saturated as well as unsaturated). Especially preferred acyl groups are octanoyl (capryloyl), nonanoyl, decanoyl, undecanoyl, undecylenoyl, dodeca-6 noyl (lauroyl), tridecanoyl, tetradecanoyl (myristyl), hexadecanoyl (palmitoyl), octadecanoyl 7 (stearoyl), oleoyl, and mixtures thereof.
8 When X is OH, the compound of Formula I represents an amino acid. According 9 to the invention, the term "amino acid" may refer to an alpha-, beta- or gamma-amino acid, i.e. n is 0, 1 or 2, but preferably is an alpha-amino acid (n is 0).
11 R' represents an amino acid side chain occurring in natural proteogenic amino 12 acids, or a side chain that is modified as compared to those occurring in natural proteogenic 13 amino acids by substitution of a hydrogen atom in the side chain for a hydroxyl, methyl, ethyl or 14 other suitable group.
A proteogenic amino acid is an amino acid that is encoded by DNA. An example 16 of a modified amino acid is hydroxyproline, occurring for instance in collagen.
17 Preferred amino acid precursors for the N-acylated compounds of Formula I
18 wherein X is OH are chosen from the group of polar amino acids, such as glutamic acid, aspar-19 tic acid, glutamine, asparagine, lysine, arginine, histidine, proline, threonine, serine. Especially preferred amino acids are glutamic acid, aspartic acid, lysine.
21 When X is a compound of Formula II, X represents an amino acid unit when m is 22 0 or a peptide when m is 1. The value of m may typically range from 1 to 18 for X to specify a 23 peptide with a molecular weight from about 200 to about 1900 Dalton.
24 Preferred peptide and/or amino acid precursors for the N-acylated compounds of Formula I are protein hydrolysates. Protein hydrolysates are degradation products of protein 26 substrates, and typically are obtained by acidic, alkaline and/or enzymatic hydrolysis of a protein 27 substrate, thereafter having an average molecular weight of 100 to 2000, preferably 100 to 1400 28 and more particularly 100 to 800. Most preferably, the protein substrate is predominantly hydro-29 lysed to the individual constituting amino acids, preferably wherein the individual amino acids constitute at least 50% (w/w) of the protein hydrolysate.
22503483.3 5 CA 2,671,471 Blakes Ref: 74537/00004 1 Suitable protein substrates for example are vegetable proteins, like wheat, rice, 2 soya, sunflower, maize, pea, almond and potato protein; animal proteins, like milk, gelatin, col-3 lagen, keratin protein; microbial proteins, like algal, yeast of fungal protein.
4 Protein substrates may be chosen based on their amino acid composition. Pref-erably, the protein substrate has a high level of glutamic acid/glutamine residues, leading to a 6 protein hydrolysate with a high glutamic acid content. An example of such a preferred protein 7 substrate is wheat protein.
8 The compounds according to Formula I are conveniently obtained by N-acylation 9 of the amino acid and/or peptide precursors as described above, using carboxylic activated de-rivatives of the fatty acid of formula RCOOH, R being defined as above, by standard methods 11 known in the art. Such derivatives are for example the symmetric anhydrides of these acids or 12 acid halides.
13 N-acylated amino acids and their salts that may be mentioned, for example, are 14 those of N-acylglutamate, such as monosodium cocoylglutamate, monosodium lauroylgluta-mate, disodium C14-C20 alkylglutamate, the C14-C20 alkyl radical being derived from 16 hydrogenated tallow, sold respectively under the names "Acylglutamate CS-11", "Acylglutamate 17 LS-11" and "Acylglutamate HS-21" by Ajinonnoto. Examples of acylglutamates also include so-18 dium cocoylglutamate and sodium laurylglutamate sold by Clariant under the Hostapon 19 CCG/CLG/KCG trade names and Protelan AG 8 (capryloylglutamate) and Protelan AGL 95 (so-dium lauroylglutamate) and Protelan AGL 5/C (sodium cocoylglutamate) of Zschimmer &
21 Schwarz.
22 Mention may also be made of N-acyl lysines such as lauroyllysine sold under the 23 name "Amihope LL" by Ajinomoto.
24 Among the N-acylated hydrolysed proteins that may be mentioned are those de-rived from all or part of collagen or keratin, such as sodium lauroyl collagen and palmitoyl 26 keratin sold under the names "Proteol B 30" and "Lipacide PK" by the company SEPPIC, or 27 from wheat, such as potassium undecylenoyl hydrolysed wheat protein sold as "Protelan AG 11"
28 by Zschimmer & Schwarz.
29 The compositions as described herein may contain mixtures of two or more of the N-acylated products mentioned above.
22503483.3 6 CA 2,671,471 Blakes Ref: 74537/00004 1 The compositions as described herein preferably has a pH in the range of 2 to 6, 2 more preferably 3 to 6, most preferably 3.5 to 5.
3 The compositions as described herein may further comprise a surfactant, such as 4 an amphoteric, an anionic, a cationic and/or a non-ionic surfactant.
Suitable amphoteric surfactants include amphoteric alkyl polyglucosides, alkyl be-6 tam, alkyl amidopropyl betaines, alkyl amidopropyl betaine amides, alkyl sulfobetaines, amine 7 oxides, amphocarboxyacetates, amphocarboxydi acetates, amphocarboxypropionates, ampho-8 carboxydipropionates, and/or derivates thereof.
9 Suitable anionic surfactants include alkylsulphates, alkylethersulphates, ami-do/amidoethersulphates, alkylsemisulphosuccinates, alkylsulphosuccinates, 11 alkylethersemisulphosuccinates, alkylethersulphosuccinates, acylamidosemisulphosuccinates, 12 acylamidosulphosuccinates, dodecylbenzenesulphonic acid, alkyl/alkylethersulphoacetates, 13 salts of sulphonated and/or sulphated organic molecules (for example, alpha-olefin sulpho-14 nates), alkyl/alkylether carboxylates, alkylphosphonates, esters of phosphoric acid, acyl isothionates, and salts thereof. Preferred anionic surfactants may be chosen from phosphoric 16 acid esters, alkylphosphonates, alkylsuphates, alkylethersulphates, alkylsulphosuccinates, al-17 kylethersulphosuccinates, as a potassium, sodium, ammonium, zinc, aluminium or 18 triethanolamine salt. Even more preferred are the zinc or aluminum salt forms.
19 Suitable cationic surfactant include skin conditioning cationic polymers, preferably from the polyquarternium-type surfactants, such as comprising MethacrylAmidoPropyl Trimethyl 21 Ammonium Chloride, DiAlly1 DiMethyl Ammonium Chloride or MethAcryloyloxethyl Trimethyl 22 Ammonium MethylSulf ate groups.
23 Suitable non-ionic surfactants include amides, ethoxylated and non-ethoxylated 24 fatty amines, ethoxylated nonylphenols, APGs (alkylpolyglucosides), AEGs (alkylethoxygluco-sides), esters/ethers of fatty acids with glycerol and/or ethoxylated and non-ethoxylated sugars, 26 ethoxylated/propoxylated and non-ethoxylated/propoxylated esters, ethoxylated/propoxylated 27 and non-ethoxylated/propoxylated fatty alcohols.
28 The compositions as described herein further may contain a carboxylic acid or a 29 salt thereof, the carboxylic acid preferably selected from the group of citric acid, glycolic acid, lactic acid, benzoic acid, salicylic acid and 2-furan carboxylic acid.
22503483.3 7 CA 2,671,471 Blakes Ref: 74537/00004 1 The compositions as described herein further may contain the usual ingredients 2 for compositions for use on the skin. For instance, the composition may include skin emollients, 3 stabilizers, pearlizing agents, thickening agents, preservatives, coloring agents or dyes and per-4 fumes.
Emollients may include glycerol, glycerides, polyglycerol, aloe vera, vitamin E, 6 sorbitol, allantoin, cationics, polymers, castor oil, lanolin and its derivatives and cetyl alcohol.
7 The composition may be thickened via the methods known to the man skilled in 8 the art, for example by addition of Sodium Chloride or a combination of Sodium Chloride and 9 specific types of surfactants (such as Sodium Lauryl Ether Sulfate or Betaines), or by addition of (hydroxy)cellulose based or (cross-) polymer based thickening agents.
Preferably, the composi-11 tion is thickened by the use of (hydroxy)cellulose based or polymer based thickening agents, 12 such as Klucel types (Hercules Chemicals), Natrosol types (Hercules Chemicals), Carbopol 13 types (Noveon), or Oxetal VD 92 of Zschimmer & Schwarz. Via these methods, and adjustment 14 of pH range, a whole range of viscosity levels may be achieved.
The composition of the present invention may be preserved by the use of pre-16 servatives which are compatible with hydrogen peroxide, such as various types of parabens, 17 benzyl alcohol, benzoic acid, potassium benzoate, salicylic acid, potassium salicylate, etc.
18 The composition of the present invention may also comprise a sequestering 19 agent, such as a cation sequestering agent chosen from ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA), N-(hydroxyethyl)-ethylenediaminetriacetic 21 acid (HEDTA), nitrilotriacetic acid (NTA), 2-hydroxyethyliminodiacetic acid (HEIDA), and salts 22 thereof or more preferably is chosen from acetanilide, trisodium ethylenediamine disuccinate, 23 phosphonic acid derivatives having 1 to 5 phosphonic acid groups, for instance a Dequest 24 phosphonate (Solutia), 1-hydroxyethylidene-1,1-diphosphonic acid (HEDP), amino tri(methylene phosphonic acid), diethylenetriamine-penta(methylene phosphonic acid), 2-hydroxy ethylimino 26 bis(methylene phosphonic acid), and ethylene diamine tetra(methylene phosphonic acid).
27 The compositions as described herein may be in the form of an aqueous solution 28 or an emulsion, such as a lotion, a foam, a liquid soap, a spray, a gel, a cream, and the like, or 29 in the form of an impregnated wipe. When the composition comprises an oil phase and a water phase, the composition does not contain the self-emulsifying base ProleIan ENS
in a concentra-31 tion of 20% (w/w).
22503483.3 8 CA 2,671,471 Blakes Ref: 74537/00004 1 In one embodiment, the composition is an aqueous solution, which can have a 2 varying degree of viscosity.
3 In a preferred embodiment, the composition is applied as a foam in order to in-4 crease contact surface and contact time and avoid spilling or dripping of the required dose off the hands, as may be the case when using a spray formulation. The use of the N-acylated ami-6 no acid in the compositions as described herein already provides foaming capacity to the 7 composition.
8 Advantageously, the compositions as described herein are able to provide ade-9 quate levels of disinfection while not being irritating to the skin or mucous membranes. The compositions are non-irritating due to the inclusion of highly skin compatible N-acylated amino 11 acids / protein hydrolysates, mild surfactant package and low concentrations of other mild addi-12 tives, which may be employed as described above. The composition has broad-spectrum 13 activity, the degree of which is unexpected given the germicidal activity of the individual ingredi-14 ents. In particular, the composition has bactericidal, fungicidal and virucidal activity. A synergy exists amongst the ingredients of the present compositions such that an effective disinfectant is 16 provided that is highly suitable for use on skin.
17 Thus, the compositions as described herein are advantageously used for all ap-18 plications where disinfection of the skin or mucous membranes may play a role. The 19 compositions may be used as an antimicrobial composition for daily use, such as in a hand soap, an antimicrobial shower gel, an impregnated wipe, or for intimate hygiene solutions. The 21 compositions may be used for preventing, regulating or curing microbial-originating skin disor-22 ders or infections, such as, but not limited to, acne, seborrhoic dermatitis, folliculitis, confluent 23 and reticulate papillomatosis and psoriatic lesions, and athlete's foot.
24 Examples Several biocidal skin compositions were prepared according to the present inven-26 tion and compared to biocidal skin compositions as known in the art, such as combinations of 27 hydrogen peroxide and betaines. The compositions were prepared in distilled water using corn-28 nnercially available concentrated stocks of the various components.
29 Explanation of the products used Protelan AG 8 Disodium Capryloyl Glutamate (Zschimmer & Schwarz) 22503483.3 9 CA 2,671,471 Blakes Ref: 74537/00004 1 Protelan AG 11 Potassium Undecylenoyl Hydrolyzed Wheat Protein (Zschimmer &
2 Schwarz) 3 Protelan AGL 95 Sodium Lauroyl Glutamate (Zschimmer & Schwarz) 4 Monafax 1214 Aliphatic Phosphoric Acid Ester (Uniqema) Texapon NSO Sodium Lauryl Ether Sulfate (Cognis) 6 Zetesol NL U Sodium Lauryl Ether Sulfate (Zschimmer & Schwarz) 7 Zetesol Zn Zinc Coceth Sulfate (Zschimmer & Schwarz) 8 Tego Betaine F Cocamidopropyl Betaine (Degussa) 9 Mackam CB 818 Cocamidopropyl Betaine (McIntyre) Octaquest Trisodium Ethylenediamine Disuccinate 12 Biocidal activity of the compositions was tested using a controlled bactericidal 13 suspension test conforming to the European Norm for chemical disinfectants and antiseptics EN
14 1276 (European Committee for Standardization, standard EN 1276:2009 -"Quantitative Sus-pension Test for the Evaluation of Bactericidal Activity of Chemical Disinfectants and Antiseptics 16 Used in Food, Industrial, Domestic, and Institutional Areas: Test Method and Requirements.").
17 One ml of a test suspension containing about 108 cfu of the test microorganism per ml is added 18 to 8 ml of the composition to be tested, and 1 ml milli-Q water is added. A clean and dirty condi-19 tion is simulated by adding bovine albumin serum (0.3% and 3.0%
respectively). After 1, 3 and 5 minutes contact time, the amount of viable bacteria was determined. The EN
1276 norm pre-21 scribes a log 5 reduction in viable cell count after a contact time of 5 minutes.
22 The results are shown in Tables 1 to 3.
23 Table 1 Composition Components 1 2 3 4 5 6 7 8 Hydrogen Peroxide 3% 3% 3% 3% 3% 3% 3% 3%
3%
Protelan AG 8 1.95% 1.95% 1.95% 1.95%
1.95%
Protelan AGL 95 1.95%
Protelan AG 11 0.72% 0.72% 0.72%
Tego Betain F50 1.52% 1.52%
1.52% 1.52% 1.52% 1.52% 1.52%
22503483.3 10 CA 2,671,471 Blakes Ref: 74537/00004 Zetesol Zn 1.25% 1.25% 1.25%
Monafax 1214 0.8%
pH (lactic acid) 4 4 4 4 4 4 4 4 4 Log reduction S. aureus 3 min. >6.6 4 >6.6 >6.6 2.2 1 >6.6 >6.6 5.2 min. >6.6 5 >6.6 >6.6 4 3 >6.6 >6.6 >6.6 S. thyphimurium 3 min >6 4 >6 >6 1 nc" >6 >6 4.6 E. colt 3 min. >6 4.6 >6 >6 3 2 >6 >6 4.8 2 * nc = not countable 4 Table 2 Composition Components 10 11 12 13 14 15 16 17 Hydrogen Peroxide 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.75%
Protelan AG 8 1.95% 1.95% 1.95% 1.95% 1.95% 1.95% 1.95% 1.95%
Protelan AG 11 0.72% 0.72% 0.72%
Tego Betain F50 1.9% 1.9% 1.9% 1.9% 1.9% 1.9%
1.9% 1.9%
Zetesol Zn 2.5% 1% 1% 1% 1%
2.25%
Texapon NSO 0.84%
1.12%
Monafax 1214 0.64% 0.64% 0.64%
EDTA
0.1% 0.15%
Octaquest 0.05% 0.05%
Na-benzoate 0.15% 0.15%
0.15%
Na-salicylate 0.1%
0.1%
Furan Carboxylic Acid 0.05%
NaCI 1%
pH (citric acid) 4 4 4 4.5 4 4 4.5
Human skin is permanently populated with a multitude of different microorgan-6 isms (bacteria, yeasts and fungi). The commensal microorganisms living on or in the skin may 7 form part of a microflora that is either resident (normal) or transient.
The resident microbial flora, 8 which is essential for good health of the skin, consists mainly of staphylococci (Staphylococcus 9 epidermis and Staphylococcus hominis), corynebacteria, Gram +
propionibacteria such as Propi-on/bacterium acnes, and also a yeast flora mainly composed of Pityrosporum ovale.
11 Pityrosporum ovale is for example believed to be involved in many skin disorders, such as seb-12 orrhoic dermatitis, folliculitis, confluent and reticulate papillomatosis and psoriatic lesions.
13 Most of the skin bacteria are present on the superficial squamous epidermis, col-14 onizing dead cells, and closely associated with the sebaceous and sweat glands. The excretions from these glands provide water, amino acids, urea, electrolytes and specific fatty 16 acids serving as nutrient elements mainly for Staphylococcus epidermidis and certain aerobic 17 corynebacteria.
18 Skin infections are usually caused by disruption of the ecological equilibrium of 19 the resident flora following colonization of the skin by pathogenic exogenous germs or following abnormal proliferation of an endogenous strain. The pathogenic germs that are the most com-21 mon are Pseudomonas aeruginosa (Gram), which is responsible for small spots, folliculitis, red 22 patches and pruritus, Candida alb/cans, which can cause inflammation at the labial angle, cuta-23 neous candidiasis, pruritus, folliculitis and aphthae, Staphylococcus aureus, which can cause 24 spots, folliculitis, impetigo and furuncles, and Group A Streptococci, responsible for impetigo.
In many industries, infection control and the prevention of spread of disease-26 causing micro-organisms is a major concern. In veterinary, healthcare, paramedical, hospitality, 27 food processing and industrial applications, the prevention of contamination with and spreading 28 of pathogenic microorganism is of crucial importance. Often, spreading of micro-organisms oc-29 curs via the hands. Viruses and bacteria on contaminated hands are easily spread among people in health care facilities such as hospitals. But also in washroom, health & wellness, 31 school and household applications, the maintenance of high hygiene standards is becoming 32 increasingly important.
22503483.3 1 CA 2,671,471 Blakes Ref: 74537/00004 1 Washing hands with detergents or soaps is a way to reduce the risk of infection.
2 However, in certain environments, such as hospitals or food processing, the required level of 3 disinfection cannot be achieved by commonly used soaps and detergents.
Consequently, hand 4 disinfectants have been developed to achieve higher levels of disinfection where the need ex-iStS.
6 Thus, this recent trend towards higher levels of infection control in hospital set-7 tings and in food & hospitality sectors, combined with the increasing awareness for infectious 8 diseases that can be transferred via the skin and respiratory system, have opted the industry to 9 come up with disinfecting compositions that can be used more frequently throughout the day.
These compositions must be hypoallergenic, non-toxic and not produce any undesirable residue 11 on the skin.
12 A problem with existing skin disinfection products, typically containing alcohols, 13 iodines/iodophors, chlorhexidine gluconate (CHG), phenolic compounds, triclosan, quaternary 14 ammonium compounds, or combinations thereof, is that they often sacrifice disinfectant activity for the sake of skin mildness or vice versa. For example, while raising the concentration of the 16 active ingredient may lead to a higher level of disinfection, such higher concentration frequently 17 leads to increased skin irritation, especially when frequently used.
Many of the currently availa-18 ble compounds cause skin dryness, skin irritation or are suspect for unwanted side-effects.
19 Many of the known and widely used skin disinfection compounds are under pressure or even banned from certain markets. This has caused the industry to come up with new solutions for 21 this problem.
22 An object of the invention is to provide an antimicrobial composition for use on 23 skin. It was found that the combination of hydrogen peroxide and N-acylated amino acids 24 and/or peptides, preferably having an acidic pH, provide for a mild yet highly effective disinfect-ant composition.
26 W092/21318 describes N-acyl derivatives of amino acids derived from cereal 27 protein hydrolysates, salts thereof, and cosmetic and detergent compositions containing said 28 derivatives or their salts.
29 EP 1 221 313 and WO 03/039496 describe detergent or cosmetic compositions having hydrating and preservative properties and simultaneously anti-dandruff and/or anti-odour 31 properties. The compositions of EP 1 221 313 comprise a salt of undecylenoil glutamate and/or 32 undecylenoil hydrolyzate of wheat and/or rice proteins and the compositions of WO 03/039496 22503483.3 2 CA 2,671,471 Blakes Ref: 74537/00004 1 include a capryloyl glutamate salt and/or capryloyl hydrolysate of wheat and/or rice protein.
2 Since such salts are able to perform also a preservative and hydrating effect, the compositions 3 do not need the addition of further preservative or hydrating agents or, at most, contain concen-4 trations thereof which are not efficacious per se. These compositions are not described for disinfecting the skin (i.e. instantly killing pathogenic micro-organisms) and are also not capable 6 of providing sufficient anti-microbial kill in sufficiently short contact times to produce an accepta-7 ble skin disinfection composition.
8 US2006/0024339 provides a method for managing redness of skin associated 9 with a dermatological condition, the method comprising topically administering to the skin of a patient a pharmaceutical composition comprising an extract of goji berries.
The pharmaceutical 11 composition used in these methods can further comprise at least one carboxylic acid. Optional-12 ly, the composition may contain various other components, among which at least one amino 13 acid or hydrogen peroxide. A useful amino acid may be N-acetylcystein.
However, the combine-14 tion of hydrogen peroxide and N-acetylcystein is not disclosed and no reference is made to the disinfecting or antimicrobial capacity of the compositions.
16 The use of lauroyl glutamate in an Emulsifying Natural System (Protelan ENS) 17 has been disclosed in a brochure of Protelan ENS (Zschimmer & Schwarz ltaliana S.p.A.; April 18 2002, BNSDOC IDNo. XP002431482). Protelan ENS is a blend of glyceryl stearate, cetearyl 19 alcohol, stearic acid and sodium lauroyl glutamate. In a series of stability and compatibility tests, an emulsion comprising 5% hydrogen peroxide in the water phase and 20%
Protelan ENS in the 21 oil phase was shown to provide a stable cream.
22 None of the prior art describes the high disinfection power of compositions as de-23 scribed herein. It was found that hydrogen peroxide and N-acylated amino acids separately 24 have low disinfection power, even in relatively high concentrations.
Only after combining hydro-gen peroxide and N-acylated amino acids in an aqueous system, a surprising synergistic effect 26 comes to effect. The synergy is highly significant and is totally unexpected when looking at the 27 performance of the two ingredients separately.
28 Thus, the present invention provides a composition for disinfecting skin compris-29 ing hydrogen peroxide in the range of 0.1-10% (w/w), preferably 0.2-6%, and an N-acylated amino acid and/or peptide in the range of 0.1-20% (w/w), preferably 0.1-10%, more preferably 31 0.2-8%, and most preferably 0.2-5% (w/w).
22503483.3 3 CA 2,671,471 Blakes Ref: 74537/00004 1 The term "N-acylated amino acid and/or peptide" according to the invention refers 2 to peptides and/or free amino acids, or salts thereof, wherein at least 50 % of the amino groups 3 of the free amino acids and/or of the peptides, is acylated. Preferably, all the amino groups are 4 acylated. The amino acid may be a single amino acid or may be a mixture of amino acids ob-tamable by hydrolysis of a suitable protein substrate. In the latter case, short peptides may be 6 present, typically comprising peptides with an average molecular weight lower than about 4000 7 Dalton, preferably lower than about 2000 Dalton.
8 The N-acylated peptide and/or N-acylated amino acid to be used according to the 9 invention preferably has a structure according to Formula I as follows:
11 R¨CO-N(H)-(CH2)n¨C(R')¨CO-X (I) 13 or a salt thereof, 14 wherein R-00- represents an acyl group wherein R is a saturated or unsaturated, straight of branched C5 to C21 radical, 16 n is 0, 1 or 2, 17 R' represents an amino acid side chain, and 18 X is OH or a group according to Formula II:
[NH¨CH(R')¨00-1, NH¨C(R')¨CO(OH) (II) 22 wherein m ranges from 0 to such a value that the compound of Formula II speci-23 fies a peptide having an average molecular weight of about 100 to about 3900 Dalton, 24 preferably of about 100 to about 1900 Dalton, more preferably about 100 to about 1300, most preferably about 100 to about 700 Dalton.
26 Suitable salts are those wherein the dissociated carboxylic groups are neutralised 27 with cations belonging to the group of alkaline metals and alkaline earth metals, ammonia, other 28 metals such as lead, iron, aluminum, manganese, copper, zinc, or by organic bases such as 22503483.3 4 CA 2,671,471 Blakes Ref: 74537/00004 1 arginine, lysine, mono-, di-, or triethanolamine, ornithine, histidine, morpholine, or choline. Such 2 neutralising cations can be utilised also in combinations with one another.
3 Preferably, the R moiety of the acyl group is a 06 to C20 radical. More preferred 4 are the straight chain variants thereof (saturated as well as unsaturated). Especially preferred acyl groups are octanoyl (capryloyl), nonanoyl, decanoyl, undecanoyl, undecylenoyl, dodeca-6 noyl (lauroyl), tridecanoyl, tetradecanoyl (myristyl), hexadecanoyl (palmitoyl), octadecanoyl 7 (stearoyl), oleoyl, and mixtures thereof.
8 When X is OH, the compound of Formula I represents an amino acid. According 9 to the invention, the term "amino acid" may refer to an alpha-, beta- or gamma-amino acid, i.e. n is 0, 1 or 2, but preferably is an alpha-amino acid (n is 0).
11 R' represents an amino acid side chain occurring in natural proteogenic amino 12 acids, or a side chain that is modified as compared to those occurring in natural proteogenic 13 amino acids by substitution of a hydrogen atom in the side chain for a hydroxyl, methyl, ethyl or 14 other suitable group.
A proteogenic amino acid is an amino acid that is encoded by DNA. An example 16 of a modified amino acid is hydroxyproline, occurring for instance in collagen.
17 Preferred amino acid precursors for the N-acylated compounds of Formula I
18 wherein X is OH are chosen from the group of polar amino acids, such as glutamic acid, aspar-19 tic acid, glutamine, asparagine, lysine, arginine, histidine, proline, threonine, serine. Especially preferred amino acids are glutamic acid, aspartic acid, lysine.
21 When X is a compound of Formula II, X represents an amino acid unit when m is 22 0 or a peptide when m is 1. The value of m may typically range from 1 to 18 for X to specify a 23 peptide with a molecular weight from about 200 to about 1900 Dalton.
24 Preferred peptide and/or amino acid precursors for the N-acylated compounds of Formula I are protein hydrolysates. Protein hydrolysates are degradation products of protein 26 substrates, and typically are obtained by acidic, alkaline and/or enzymatic hydrolysis of a protein 27 substrate, thereafter having an average molecular weight of 100 to 2000, preferably 100 to 1400 28 and more particularly 100 to 800. Most preferably, the protein substrate is predominantly hydro-29 lysed to the individual constituting amino acids, preferably wherein the individual amino acids constitute at least 50% (w/w) of the protein hydrolysate.
22503483.3 5 CA 2,671,471 Blakes Ref: 74537/00004 1 Suitable protein substrates for example are vegetable proteins, like wheat, rice, 2 soya, sunflower, maize, pea, almond and potato protein; animal proteins, like milk, gelatin, col-3 lagen, keratin protein; microbial proteins, like algal, yeast of fungal protein.
4 Protein substrates may be chosen based on their amino acid composition. Pref-erably, the protein substrate has a high level of glutamic acid/glutamine residues, leading to a 6 protein hydrolysate with a high glutamic acid content. An example of such a preferred protein 7 substrate is wheat protein.
8 The compounds according to Formula I are conveniently obtained by N-acylation 9 of the amino acid and/or peptide precursors as described above, using carboxylic activated de-rivatives of the fatty acid of formula RCOOH, R being defined as above, by standard methods 11 known in the art. Such derivatives are for example the symmetric anhydrides of these acids or 12 acid halides.
13 N-acylated amino acids and their salts that may be mentioned, for example, are 14 those of N-acylglutamate, such as monosodium cocoylglutamate, monosodium lauroylgluta-mate, disodium C14-C20 alkylglutamate, the C14-C20 alkyl radical being derived from 16 hydrogenated tallow, sold respectively under the names "Acylglutamate CS-11", "Acylglutamate 17 LS-11" and "Acylglutamate HS-21" by Ajinonnoto. Examples of acylglutamates also include so-18 dium cocoylglutamate and sodium laurylglutamate sold by Clariant under the Hostapon 19 CCG/CLG/KCG trade names and Protelan AG 8 (capryloylglutamate) and Protelan AGL 95 (so-dium lauroylglutamate) and Protelan AGL 5/C (sodium cocoylglutamate) of Zschimmer &
21 Schwarz.
22 Mention may also be made of N-acyl lysines such as lauroyllysine sold under the 23 name "Amihope LL" by Ajinomoto.
24 Among the N-acylated hydrolysed proteins that may be mentioned are those de-rived from all or part of collagen or keratin, such as sodium lauroyl collagen and palmitoyl 26 keratin sold under the names "Proteol B 30" and "Lipacide PK" by the company SEPPIC, or 27 from wheat, such as potassium undecylenoyl hydrolysed wheat protein sold as "Protelan AG 11"
28 by Zschimmer & Schwarz.
29 The compositions as described herein may contain mixtures of two or more of the N-acylated products mentioned above.
22503483.3 6 CA 2,671,471 Blakes Ref: 74537/00004 1 The compositions as described herein preferably has a pH in the range of 2 to 6, 2 more preferably 3 to 6, most preferably 3.5 to 5.
3 The compositions as described herein may further comprise a surfactant, such as 4 an amphoteric, an anionic, a cationic and/or a non-ionic surfactant.
Suitable amphoteric surfactants include amphoteric alkyl polyglucosides, alkyl be-6 tam, alkyl amidopropyl betaines, alkyl amidopropyl betaine amides, alkyl sulfobetaines, amine 7 oxides, amphocarboxyacetates, amphocarboxydi acetates, amphocarboxypropionates, ampho-8 carboxydipropionates, and/or derivates thereof.
9 Suitable anionic surfactants include alkylsulphates, alkylethersulphates, ami-do/amidoethersulphates, alkylsemisulphosuccinates, alkylsulphosuccinates, 11 alkylethersemisulphosuccinates, alkylethersulphosuccinates, acylamidosemisulphosuccinates, 12 acylamidosulphosuccinates, dodecylbenzenesulphonic acid, alkyl/alkylethersulphoacetates, 13 salts of sulphonated and/or sulphated organic molecules (for example, alpha-olefin sulpho-14 nates), alkyl/alkylether carboxylates, alkylphosphonates, esters of phosphoric acid, acyl isothionates, and salts thereof. Preferred anionic surfactants may be chosen from phosphoric 16 acid esters, alkylphosphonates, alkylsuphates, alkylethersulphates, alkylsulphosuccinates, al-17 kylethersulphosuccinates, as a potassium, sodium, ammonium, zinc, aluminium or 18 triethanolamine salt. Even more preferred are the zinc or aluminum salt forms.
19 Suitable cationic surfactant include skin conditioning cationic polymers, preferably from the polyquarternium-type surfactants, such as comprising MethacrylAmidoPropyl Trimethyl 21 Ammonium Chloride, DiAlly1 DiMethyl Ammonium Chloride or MethAcryloyloxethyl Trimethyl 22 Ammonium MethylSulf ate groups.
23 Suitable non-ionic surfactants include amides, ethoxylated and non-ethoxylated 24 fatty amines, ethoxylated nonylphenols, APGs (alkylpolyglucosides), AEGs (alkylethoxygluco-sides), esters/ethers of fatty acids with glycerol and/or ethoxylated and non-ethoxylated sugars, 26 ethoxylated/propoxylated and non-ethoxylated/propoxylated esters, ethoxylated/propoxylated 27 and non-ethoxylated/propoxylated fatty alcohols.
28 The compositions as described herein further may contain a carboxylic acid or a 29 salt thereof, the carboxylic acid preferably selected from the group of citric acid, glycolic acid, lactic acid, benzoic acid, salicylic acid and 2-furan carboxylic acid.
22503483.3 7 CA 2,671,471 Blakes Ref: 74537/00004 1 The compositions as described herein further may contain the usual ingredients 2 for compositions for use on the skin. For instance, the composition may include skin emollients, 3 stabilizers, pearlizing agents, thickening agents, preservatives, coloring agents or dyes and per-4 fumes.
Emollients may include glycerol, glycerides, polyglycerol, aloe vera, vitamin E, 6 sorbitol, allantoin, cationics, polymers, castor oil, lanolin and its derivatives and cetyl alcohol.
7 The composition may be thickened via the methods known to the man skilled in 8 the art, for example by addition of Sodium Chloride or a combination of Sodium Chloride and 9 specific types of surfactants (such as Sodium Lauryl Ether Sulfate or Betaines), or by addition of (hydroxy)cellulose based or (cross-) polymer based thickening agents.
Preferably, the composi-11 tion is thickened by the use of (hydroxy)cellulose based or polymer based thickening agents, 12 such as Klucel types (Hercules Chemicals), Natrosol types (Hercules Chemicals), Carbopol 13 types (Noveon), or Oxetal VD 92 of Zschimmer & Schwarz. Via these methods, and adjustment 14 of pH range, a whole range of viscosity levels may be achieved.
The composition of the present invention may be preserved by the use of pre-16 servatives which are compatible with hydrogen peroxide, such as various types of parabens, 17 benzyl alcohol, benzoic acid, potassium benzoate, salicylic acid, potassium salicylate, etc.
18 The composition of the present invention may also comprise a sequestering 19 agent, such as a cation sequestering agent chosen from ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA), N-(hydroxyethyl)-ethylenediaminetriacetic 21 acid (HEDTA), nitrilotriacetic acid (NTA), 2-hydroxyethyliminodiacetic acid (HEIDA), and salts 22 thereof or more preferably is chosen from acetanilide, trisodium ethylenediamine disuccinate, 23 phosphonic acid derivatives having 1 to 5 phosphonic acid groups, for instance a Dequest 24 phosphonate (Solutia), 1-hydroxyethylidene-1,1-diphosphonic acid (HEDP), amino tri(methylene phosphonic acid), diethylenetriamine-penta(methylene phosphonic acid), 2-hydroxy ethylimino 26 bis(methylene phosphonic acid), and ethylene diamine tetra(methylene phosphonic acid).
27 The compositions as described herein may be in the form of an aqueous solution 28 or an emulsion, such as a lotion, a foam, a liquid soap, a spray, a gel, a cream, and the like, or 29 in the form of an impregnated wipe. When the composition comprises an oil phase and a water phase, the composition does not contain the self-emulsifying base ProleIan ENS
in a concentra-31 tion of 20% (w/w).
22503483.3 8 CA 2,671,471 Blakes Ref: 74537/00004 1 In one embodiment, the composition is an aqueous solution, which can have a 2 varying degree of viscosity.
3 In a preferred embodiment, the composition is applied as a foam in order to in-4 crease contact surface and contact time and avoid spilling or dripping of the required dose off the hands, as may be the case when using a spray formulation. The use of the N-acylated ami-6 no acid in the compositions as described herein already provides foaming capacity to the 7 composition.
8 Advantageously, the compositions as described herein are able to provide ade-9 quate levels of disinfection while not being irritating to the skin or mucous membranes. The compositions are non-irritating due to the inclusion of highly skin compatible N-acylated amino 11 acids / protein hydrolysates, mild surfactant package and low concentrations of other mild addi-12 tives, which may be employed as described above. The composition has broad-spectrum 13 activity, the degree of which is unexpected given the germicidal activity of the individual ingredi-14 ents. In particular, the composition has bactericidal, fungicidal and virucidal activity. A synergy exists amongst the ingredients of the present compositions such that an effective disinfectant is 16 provided that is highly suitable for use on skin.
17 Thus, the compositions as described herein are advantageously used for all ap-18 plications where disinfection of the skin or mucous membranes may play a role. The 19 compositions may be used as an antimicrobial composition for daily use, such as in a hand soap, an antimicrobial shower gel, an impregnated wipe, or for intimate hygiene solutions. The 21 compositions may be used for preventing, regulating or curing microbial-originating skin disor-22 ders or infections, such as, but not limited to, acne, seborrhoic dermatitis, folliculitis, confluent 23 and reticulate papillomatosis and psoriatic lesions, and athlete's foot.
24 Examples Several biocidal skin compositions were prepared according to the present inven-26 tion and compared to biocidal skin compositions as known in the art, such as combinations of 27 hydrogen peroxide and betaines. The compositions were prepared in distilled water using corn-28 nnercially available concentrated stocks of the various components.
29 Explanation of the products used Protelan AG 8 Disodium Capryloyl Glutamate (Zschimmer & Schwarz) 22503483.3 9 CA 2,671,471 Blakes Ref: 74537/00004 1 Protelan AG 11 Potassium Undecylenoyl Hydrolyzed Wheat Protein (Zschimmer &
2 Schwarz) 3 Protelan AGL 95 Sodium Lauroyl Glutamate (Zschimmer & Schwarz) 4 Monafax 1214 Aliphatic Phosphoric Acid Ester (Uniqema) Texapon NSO Sodium Lauryl Ether Sulfate (Cognis) 6 Zetesol NL U Sodium Lauryl Ether Sulfate (Zschimmer & Schwarz) 7 Zetesol Zn Zinc Coceth Sulfate (Zschimmer & Schwarz) 8 Tego Betaine F Cocamidopropyl Betaine (Degussa) 9 Mackam CB 818 Cocamidopropyl Betaine (McIntyre) Octaquest Trisodium Ethylenediamine Disuccinate 12 Biocidal activity of the compositions was tested using a controlled bactericidal 13 suspension test conforming to the European Norm for chemical disinfectants and antiseptics EN
14 1276 (European Committee for Standardization, standard EN 1276:2009 -"Quantitative Sus-pension Test for the Evaluation of Bactericidal Activity of Chemical Disinfectants and Antiseptics 16 Used in Food, Industrial, Domestic, and Institutional Areas: Test Method and Requirements.").
17 One ml of a test suspension containing about 108 cfu of the test microorganism per ml is added 18 to 8 ml of the composition to be tested, and 1 ml milli-Q water is added. A clean and dirty condi-19 tion is simulated by adding bovine albumin serum (0.3% and 3.0%
respectively). After 1, 3 and 5 minutes contact time, the amount of viable bacteria was determined. The EN
1276 norm pre-21 scribes a log 5 reduction in viable cell count after a contact time of 5 minutes.
22 The results are shown in Tables 1 to 3.
23 Table 1 Composition Components 1 2 3 4 5 6 7 8 Hydrogen Peroxide 3% 3% 3% 3% 3% 3% 3% 3%
3%
Protelan AG 8 1.95% 1.95% 1.95% 1.95%
1.95%
Protelan AGL 95 1.95%
Protelan AG 11 0.72% 0.72% 0.72%
Tego Betain F50 1.52% 1.52%
1.52% 1.52% 1.52% 1.52% 1.52%
22503483.3 10 CA 2,671,471 Blakes Ref: 74537/00004 Zetesol Zn 1.25% 1.25% 1.25%
Monafax 1214 0.8%
pH (lactic acid) 4 4 4 4 4 4 4 4 4 Log reduction S. aureus 3 min. >6.6 4 >6.6 >6.6 2.2 1 >6.6 >6.6 5.2 min. >6.6 5 >6.6 >6.6 4 3 >6.6 >6.6 >6.6 S. thyphimurium 3 min >6 4 >6 >6 1 nc" >6 >6 4.6 E. colt 3 min. >6 4.6 >6 >6 3 2 >6 >6 4.8 2 * nc = not countable 4 Table 2 Composition Components 10 11 12 13 14 15 16 17 Hydrogen Peroxide 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.75%
Protelan AG 8 1.95% 1.95% 1.95% 1.95% 1.95% 1.95% 1.95% 1.95%
Protelan AG 11 0.72% 0.72% 0.72%
Tego Betain F50 1.9% 1.9% 1.9% 1.9% 1.9% 1.9%
1.9% 1.9%
Zetesol Zn 2.5% 1% 1% 1% 1%
2.25%
Texapon NSO 0.84%
1.12%
Monafax 1214 0.64% 0.64% 0.64%
EDTA
0.1% 0.15%
Octaquest 0.05% 0.05%
Na-benzoate 0.15% 0.15%
0.15%
Na-salicylate 0.1%
0.1%
Furan Carboxylic Acid 0.05%
NaCI 1%
pH (citric acid) 4 4 4 4.5 4 4 4.5
5.5 Log reduction S. aureus 3 min. 4.4 5.4 >6.6 5.6 4.8 5.6 ->6.6 >6.6 5 min. >6.6 >6.6 >6.6 >6.6 >6.6 >6.6 >6.6 >6.6 22503483.3 11 CA 2,671,471 Blakes Ref: 74537/00004 1 Table 3 Composition Components 18 19 20 21 22 23 24 25 Hydrogen Peroxide 2% 2.5% 2.5% 2.5% 2%
2% 2% 2%
Protelan AG 8 2.35% 1.95% 1.95% 1.95%
3.12% 1.95% 3.12%
Mackam CB 818 1% 2% 1.9% 1.9%
1.9% 1.9% 1.9%
Zetesol NL U
3.35% 3.35% 4.20% 4.20% 3.35% 3.35% 3.35% 3.35%
Glycerine 1% 1% 2% 2% 1% 1% 1% 1%
Na-benzoate 0.15% 0.15%
Na-salicylate 0.1% 0.1%
pH (lactic acid) 4 4 3.5 3.5 4 4 4 4.5 Log reduction E. co/il min. >5 >5 >5 >5 1.1 >6 >6 >6 S. aureus 1 min. >5 >5 >5 >5 2.3 >6 >6 >5 3 Compositions 1 to 4, 7 to 21 and 23 to 25 are compositions according to the pre-4 sent invention. These compositions show high antimicrobial efficacy, especially where the composition is further completed with an anionic or amphoteric surfactant. The compositions 18
2% 2% 2%
Protelan AG 8 2.35% 1.95% 1.95% 1.95%
3.12% 1.95% 3.12%
Mackam CB 818 1% 2% 1.9% 1.9%
1.9% 1.9% 1.9%
Zetesol NL U
3.35% 3.35% 4.20% 4.20% 3.35% 3.35% 3.35% 3.35%
Glycerine 1% 1% 2% 2% 1% 1% 1% 1%
Na-benzoate 0.15% 0.15%
Na-salicylate 0.1% 0.1%
pH (lactic acid) 4 4 3.5 3.5 4 4 4 4.5 Log reduction E. co/il min. >5 >5 >5 >5 1.1 >6 >6 >6 S. aureus 1 min. >5 >5 >5 >5 2.3 >6 >6 >5 3 Compositions 1 to 4, 7 to 21 and 23 to 25 are compositions according to the pre-4 sent invention. These compositions show high antimicrobial efficacy, especially where the composition is further completed with an anionic or amphoteric surfactant. The compositions 18
6 to 21 even passed the norm (> log 5 reduction) on all test organisms Escherichia coli, Pseudo-
7 monas aeruginosa, Staphylococcus aureus, and Enterococcus hirae within only 1 minute
8 contact time, in both simulated clean and dirty conditions.
9 Compositions 5, 6 and 22 are compositions which are not according to this inven-tion and show substantially less or no antimicrobial activity. These examples clearly show that 11 hydrogen peroxide itself does not have sufficient disinfection capacity and that the compositions 12 containing hydrogen peroxide and an N-acylated amino acid are, surprisingly, highly effective.
13 In order to further evidence the influence of other surfactants in the compositions, 14 composition 3, 4 and 24 were prepared. These compositions do not contain cocamidopropyl betaine, a surfactant with slight biocidal characteristics, and were shown to pass the EN 1276 16 norm. A comparison of compositions 22 and 24 further evidences that the influence of cocami-17 dopropyl betaine on the efficacy of the composition is not present indeed.
18 The compositions 18 to 21 also pass the European Norm for hygienic hand wash-19 ing, EN 1499 (European Committee for Standardization, standard EN
1499:1997 - "Chemical Disinfectants and Antiseptics - Hygienic Handwash: Test Method and Requirements.") with only 22503483.3 12 CA 2,671,471 Blakes Ref: 74537/00004 1 30 seconds contact time. A composition without either hydrogen peroxide or the N-acylated 2 amino acid failed the test, even with a contact time of 60 seconds.
3 Surprisingly, the compositions as described herein have also virucidal efficacy.
4 Compositions 18 to 21 have shown to kill enveloped blood borne viruses on model viruses bo-vine viral diarrhea virus (BVDV) and vaccinia virus in a controlled virucidal suspension test with 6 a contact time of only 30 seconds. Efficacy against both BVDV and vaccinia provides, under 7 accepted German standards (Announcement of the Federal Health Office (1982): Directive of 8 the Federal Health Office and the German Association for the Control of Virus Diseases for the 9 testing of chemical disinfectants for efficacy against viruses. Federal Health Journal 25: 397-398; and, Notice of the Technical Committee "Virus disinfection" of the German Association for 11 the Control of Virus Diseases and the Robert Koch Institute (2003), Federal Health Bulletin 46:
12 619), for an effect against all enveloped blood borne viruses, such as HIV, HCV, HBV, Human 13 Influenza, H5N1 and SARS (tested at Mikrolab GmbH, Dr. J. Steinmann).
14 Compositions 18 to 21 have been tested in a controlled dermatological skin patch test for 48 hours and 72 hours on 50 persons with different skin conditions:
25 with normal 16 healthy skin, 5 with eczema, 1 with allergic skin, and 19 with sensitive skin. The compositions 17 18 to 21 have been compared to a 1% dilution of Sodium Dodecyl Sulfate (SDS) in water and 18 were scored on erythema, fissure, and scaling. The SDS solution showed clear irritation in 12 19 cases. With the compositions 18 to 21, after both 48 hours and 72 hours, none of the subjects showed any redness or irritation of the skin. These test results clearly evidence that the broad 21 spectrum and highly bactericidal compositions 18 to 21 were surprisingly mild to the skin.
22 Important to notice is that bactericidal activity is not the only important variable in 23 the biocidal skin compositions as described herein. It was also found that the compositions are 24 extremely skin friendly and leave the user with a soft and well-cared afterf eel. Skin feel, dirt and sebum removal, lathering effect, moisturisation of the skin, non-stickiness and skin afterf eel 26 should all be considered, together with the bactericidal effect, to arrive at an efficacious compo-27 sition.
28 The scope of the claims appended hereto should not be limited by the preferred 29 embodiments set forth in the present description, but should be given the broadest interpretation consistent with the description as a whole.
22503483.3 13
13 In order to further evidence the influence of other surfactants in the compositions, 14 composition 3, 4 and 24 were prepared. These compositions do not contain cocamidopropyl betaine, a surfactant with slight biocidal characteristics, and were shown to pass the EN 1276 16 norm. A comparison of compositions 22 and 24 further evidences that the influence of cocami-17 dopropyl betaine on the efficacy of the composition is not present indeed.
18 The compositions 18 to 21 also pass the European Norm for hygienic hand wash-19 ing, EN 1499 (European Committee for Standardization, standard EN
1499:1997 - "Chemical Disinfectants and Antiseptics - Hygienic Handwash: Test Method and Requirements.") with only 22503483.3 12 CA 2,671,471 Blakes Ref: 74537/00004 1 30 seconds contact time. A composition without either hydrogen peroxide or the N-acylated 2 amino acid failed the test, even with a contact time of 60 seconds.
3 Surprisingly, the compositions as described herein have also virucidal efficacy.
4 Compositions 18 to 21 have shown to kill enveloped blood borne viruses on model viruses bo-vine viral diarrhea virus (BVDV) and vaccinia virus in a controlled virucidal suspension test with 6 a contact time of only 30 seconds. Efficacy against both BVDV and vaccinia provides, under 7 accepted German standards (Announcement of the Federal Health Office (1982): Directive of 8 the Federal Health Office and the German Association for the Control of Virus Diseases for the 9 testing of chemical disinfectants for efficacy against viruses. Federal Health Journal 25: 397-398; and, Notice of the Technical Committee "Virus disinfection" of the German Association for 11 the Control of Virus Diseases and the Robert Koch Institute (2003), Federal Health Bulletin 46:
12 619), for an effect against all enveloped blood borne viruses, such as HIV, HCV, HBV, Human 13 Influenza, H5N1 and SARS (tested at Mikrolab GmbH, Dr. J. Steinmann).
14 Compositions 18 to 21 have been tested in a controlled dermatological skin patch test for 48 hours and 72 hours on 50 persons with different skin conditions:
25 with normal 16 healthy skin, 5 with eczema, 1 with allergic skin, and 19 with sensitive skin. The compositions 17 18 to 21 have been compared to a 1% dilution of Sodium Dodecyl Sulfate (SDS) in water and 18 were scored on erythema, fissure, and scaling. The SDS solution showed clear irritation in 12 19 cases. With the compositions 18 to 21, after both 48 hours and 72 hours, none of the subjects showed any redness or irritation of the skin. These test results clearly evidence that the broad 21 spectrum and highly bactericidal compositions 18 to 21 were surprisingly mild to the skin.
22 Important to notice is that bactericidal activity is not the only important variable in 23 the biocidal skin compositions as described herein. It was also found that the compositions are 24 extremely skin friendly and leave the user with a soft and well-cared afterf eel. Skin feel, dirt and sebum removal, lathering effect, moisturisation of the skin, non-stickiness and skin afterf eel 26 should all be considered, together with the bactericidal effect, to arrive at an efficacious compo-27 sition.
28 The scope of the claims appended hereto should not be limited by the preferred 29 embodiments set forth in the present description, but should be given the broadest interpretation consistent with the description as a whole.
22503483.3 13
Claims (27)
1. A composition for skin disinfection comprising: 0.1 to 10% (w/w) hydrogen peroxide; and, 0.1 to 20% (w/w) N-acylated amino acid and/or peptide, or a salt thereof;
wherein, when the composition comprises an oil phase and a water phase, the composition does not contain a self-emulsifying base ProleIan ENS, which is blend of glyceryl stearate, cetearyl alcohol, stearic acid and sodium lauroyl glutamate, in a concentration of 20% (w/w).
wherein, when the composition comprises an oil phase and a water phase, the composition does not contain a self-emulsifying base ProleIan ENS, which is blend of glyceryl stearate, cetearyl alcohol, stearic acid and sodium lauroyl glutamate, in a concentration of 20% (w/w).
2. The composition of claim 1, wherein the hydrogen peroxide is present in a concentration of 0.2-6% (w/w).
3. The composition of claim 1 or 2, wherein the N-acylated amino acid and/or peptide, or a salt thereof is present in a concentration of 0.1 to 10%.
4. The composition of claim 1 or 2, wherein the N-acylated amino acid and/or peptide, or a salt thereof is present in a concentration of 0.2 to 8%.
5. The composition of claim 1 or 2, wherein the N-acylated amino acid and/or peptide, or a salt thereof is present in a concentration of 0.2 to 5%.
6. The composition of any one of claims 1-5 which is an aqueous solution.
7. The composition of any one of claims 1-6 having a pH in the range of 2 to 6.
8. The composition of claim 7, wherein the composition has a pH of 3 to 6.
9. The composition of claim 7, wherein the composition has a pH of 3.5 to 5.
10. The composition of any one of claims 1-9, wherein the N-acylated amino acid and/or peptide comprises an acyl radical having between 5 and 21 carbon atoms.
11. The composition of any one of claims 1-10, wherein the N-acylated amino acid and/or peptide is an N-acylated polar amino acid.
12. The composition of claim 11, wherein the N-acylated polar amino acid is an N-acylated glutamic acid.
13. The composition of any one of claims 1-12, wherein the N-acylated amino acid and/or peptide is an N-acylated wheat protein hydrolysate.
14. The composition of any one of claims 1-12 further comprising an amphoteric, anionic, cationic and/or non-ionic surfactant.
15. The composition of claim 14, wherein the amphoteric surfactant is chosen from amphoteric alkyl polyglucosides, alkyl betaines, alkyl amidopropyl betaines, alkyl amidopropyl betaine amides, alkyl sulfobetaines, amine oxides, amphocarboxyacetates, amphocarboxydiacetates, amphocarboxypropionates, amphocarboxydipropionates, and derivates thereof.
16. The composition of claim 14, wherein the anionic surfactant is chosen from alkylsulphates, alkylethersulphates, amido/amidoethersulphates, alkylsemisulphosuccinates, alkylsulphosuccinates, alkylethersemisulphosuccinates, alkylethersulphosuccinates, acylamidosemisulphosuccinates, acylamidosulphosuccinates, dodecylbenzenesulphonic acid, alkyl/alkylethersulphoacetates, salts of sulphonated and/or sulphated organic molecules, alkyl/alkylether carboxylates, alkylphosphonates, esters of phosphoric acid, acyl isothionates, and salts thereof.
17. The composition of claim 14, wherein the cationic surfactant is chosen from skin conditioning cationic polymers.
18. The composition of claim 14, wherein cationic surfactant is chosen from polyquarternium-type surfactants.
19. The composition of claim 14, wherein the nonionic surfactant is chosen from:
amides;
ethoxylated and non-ethoxylated fatty amines;
ethoxylated nonylphenols;
APGs (alkylpolyglucosides);
AEGs (alkylethoxyglucosides);
esters/ethers of fatty acids with glycerol and/or ethoxylated and non-ethoxylated sugars;
ethoxylated/propoxylated and non-ethoxylated/propoxylated esters; and, ethoxylated/propoxylated and non-ethoxylated/propoxylated fatty alcohols.
amides;
ethoxylated and non-ethoxylated fatty amines;
ethoxylated nonylphenols;
APGs (alkylpolyglucosides);
AEGs (alkylethoxyglucosides);
esters/ethers of fatty acids with glycerol and/or ethoxylated and non-ethoxylated sugars;
ethoxylated/propoxylated and non-ethoxylated/propoxylated esters; and, ethoxylated/propoxylated and non-ethoxylated/propoxylated fatty alcohols.
20. The composition of any one of claims 1-19 further comprising a carboxylic acid or a salt thereof.
21. The composition of claim 20, wherein the carboxylic acid is chosen from citric acid, glycolic acid, lactic acid, benzoic acid, salicylic acid, and 2-furan carboxylic acid.
22. The composition of any one of the claims 1-21 further comprising a skin emollient.
23. The composition of claim 22, wherein the skin emollient is chosen from glycerol, glycerides, polyglycerol, aloe vera, vitamin E, sorbitol, allantoin, cationics, polymers, castor oil, lanolin and its derivatives and cetyl alcohol.
24. The composition of any one of claims 1-23 further comprising stabilizers, pearlizing agents, thickening agents, preservatives, coloring agents or dyes and perfumes.
25. Use of the composition as defined in any one of claims 1-24 for disinfection of the skin or mucous membranes.
26. Use of the composition as defined in any one of claims 1-24 as an antimicrobial composition for daily use.
27. Use of the composition as defined in any one of claims 1-24 for preventing, regulating or curing skin infections or skin disorders.
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EP06126044 | 2006-12-13 | ||
PCT/EP2007/063831 WO2008071746A1 (en) | 2006-12-13 | 2007-12-12 | Mild composition for skin disinfection |
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CA2671471A1 CA2671471A1 (en) | 2008-06-19 |
CA2671471C true CA2671471C (en) | 2015-11-03 |
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EP (1) | EP2101720B1 (en) |
JP (1) | JP5438518B2 (en) |
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US8383164B2 (en) * | 2009-06-29 | 2013-02-26 | Innovasource Llc | Antiviral composition and method for using the same |
JP5508053B2 (en) * | 2010-02-18 | 2014-05-28 | 旭化成ケミカルズ株式会社 | Fungicide |
MX2012014376A (en) * | 2010-06-07 | 2013-01-22 | Stepan Co | Dilutable biocidal compositions and methods of use. |
US20130089621A1 (en) | 2011-10-05 | 2013-04-11 | Arkema Inc. | Disinfectant compositions with hydrogen peroxide |
US20130089533A1 (en) | 2011-10-05 | 2013-04-11 | Arkema Inc. | Disinfectant compositions with hydrogen peroxide |
EA022773B1 (en) * | 2012-05-24 | 2016-02-29 | Ооо "Научно-Производственный Центр Химмедсинтез" | Disinfecting composition |
FR2992859B1 (en) * | 2012-07-09 | 2014-10-03 | Fabre Pierre Dermo Cosmetique | USE OF COCETH ZINC SULFATE AS ANTIBACTERIAL AGENT AFTER PROPIONIBACTERIUM ACNES |
CN103520022B (en) * | 2013-10-21 | 2015-12-23 | 广州立白企业集团有限公司 | A kind of bacteriostatic hand sanitizer and preparation method thereof |
JP6162579B2 (en) * | 2013-11-14 | 2017-07-12 | 雪印メグミルク株式会社 | New bacteriostatic or antibacterial agent |
BR112017016729B1 (en) * | 2015-02-05 | 2022-09-13 | Hygienix Bv | METHOD FOR DISINFECTING A SURFACE AND SUITABLE COMPOSITION FOR USE ON IT |
CA2991917A1 (en) | 2015-07-17 | 2017-01-26 | Colgate-Palmolive Company | Oral care compositions |
RU2636496C1 (en) * | 2016-08-18 | 2017-11-23 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский технологический университет" | Antimicrobial universal soap based on hydrogen peroxide with high stability |
RU2669343C2 (en) * | 2016-12-14 | 2018-10-10 | федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный технический университет" | Disinfecting composition |
BR112019016988B1 (en) * | 2017-02-17 | 2023-02-23 | Diversey, Inc | PEROXIDE-BASED DISINFECTING SOLUTIONS CONTAINING INORGANIC SALTS, METHOD FOR DISINFECTING OR SANITIZING A SURFACE |
CN108477209B (en) * | 2018-05-30 | 2021-01-15 | 军事科学院***工程研究院卫勤保障技术研究所 | Disinfectant and preparation method thereof |
WO2020139586A1 (en) * | 2018-12-28 | 2020-07-02 | Diversey, Inc. | Synergistic disinfectant compositions having enhanced antimicrobial efficacy and stability, and methods of using the same |
WO2020167933A1 (en) | 2019-02-12 | 2020-08-20 | Alden Medical, Llc | Alcohol-free hydrogen peroxide disinfectant compositions and methods of use thereof |
SE544655C2 (en) * | 2020-11-18 | 2022-10-04 | Lantmaennen Oats Ab | Anti-microbial skin-care composition comprising beta-glucan, hydrogen peroxide and lactic acid |
CN114287451B (en) * | 2021-12-31 | 2022-12-27 | 上海纳米技术及应用国家工程研究中心有限公司 | Preparation method of natural plant modified antibacterial liquid and product thereof |
JP7315263B1 (en) | 2022-06-17 | 2023-07-26 | 株式会社ニイタカ | Virus inactivating composition, disinfectant, cleaning agent, and sanitary material |
WO2024074910A1 (en) * | 2022-10-07 | 2024-04-11 | 3M Innovative Properties Company | Biocidal composition |
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US4477438A (en) | 1982-11-12 | 1984-10-16 | Surgikos, Inc. | Hydrogen peroxide composition |
FR2676922B1 (en) * | 1991-06-03 | 1995-01-20 | Givaudan Lavirotte | COSMETIC APPLICATIONS OF N-ACYL DERIVATIVES OF MIXTURES OF AMINO ACIDS DERIVED FROM VEGETABLE PROTEIN HYDROLYSATES. |
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CN1268162A (en) * | 1997-07-09 | 2000-09-27 | 普罗格特-甘布尔公司 | Cleaning compositions comprising an oxidoreductase |
DE19815972C1 (en) | 1998-04-09 | 1999-09-30 | Goldwell Gmbh | Fast-acting permanent wave fixative with conditioning effect on hair |
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EP1129701A1 (en) | 2000-02-29 | 2001-09-05 | Primacare S.A. | Cosmetic compositions comprising a chemiluminescence compound |
EP1221313A3 (en) | 2001-01-09 | 2003-11-26 | Zschimmer & Schwarz Italiana S.p.A. | Salts of undecylenoyl glutamate or of undecylenoyl hydrolyzate of wheat or rice proteins in detergent or cosmetic compositions |
ITTO20011053A1 (en) | 2001-11-07 | 2003-05-07 | Zschimmer E Schwarz Italiana S | USE OF GLUTAMATED CAPRILOIL E-OR HYDROLY CAPRILOIL SALTS OF E-OR RICE WHEAT PROTEINS IN THE FORMULATION OF DETERGENT OR DETERGENT COMPOSITIONS |
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US20060024339A1 (en) * | 2004-07-29 | 2006-02-02 | Howard Murad | Methods of managing the redness associated with a dermatological condition |
EP2041254B1 (en) | 2006-07-06 | 2012-11-07 | Centennial Ventures BV | Broad spectrum and skin friendly disinfecting composition |
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CN101553202A (en) | 2009-10-07 |
CN101553202B (en) | 2015-07-22 |
RU2009121450A (en) | 2011-01-20 |
DK2101720T3 (en) | 2016-06-13 |
EP2101720B1 (en) | 2016-03-23 |
EP2101720A1 (en) | 2009-09-23 |
AU2007331481B2 (en) | 2012-12-20 |
JP5438518B2 (en) | 2014-03-12 |
WO2008071746A1 (en) | 2008-06-19 |
AU2007331481A1 (en) | 2008-06-19 |
CA2671471A1 (en) | 2008-06-19 |
BRPI0720201B1 (en) | 2016-03-29 |
ES2570599T3 (en) | 2016-05-19 |
US20100028458A1 (en) | 2010-02-04 |
HK1136966A1 (en) | 2010-07-16 |
RU2441644C2 (en) | 2012-02-10 |
BRPI0720201A2 (en) | 2013-12-31 |
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